Synthesis and oxidation of chiral 2-thiazolines (4, 5-dihydro-1, 3-thiazoles)

…, DP Armstrong, RHB Galt, STE Mesher

Index: Aitken, R. Alan; Armstrong, David P.; Galt, Ronald H. B.; Mesher, Shaun T. E. Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 6 p. 935 - 943

Full Text: HTML

Citation Number: 27

Abstract

Eight new chiral 2-thiazolines (4, 5-dihydro-1, 3-thiazoles) 2 have been prepared by treatment of the 2-methyloxazolines 1, the benzoylamino alcohols 4 or the trimethylacetylamino alcohols 5 with P2S5. With a 2-methyl substituent, reaction with Oxone® results in ring-opening to give the acetylamino disulfides 9 and with MCPBA there is also ring-opening with incorporation of a m-chlorobenzoyl group to give 12. Treatment ...